Harper Insure is an AI-native commercial insurance brokerage that automates and accelerates the process of securing business coverage.
SALES DEVELOPMENT REPRESENTATIVE, AI-NATIVE Harper is an AI-native commercial insurance company in San Francisco. We're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown roughly 100x in the last year and we move at that speed: on-site, in person, long days, very high standards. THE ROLE This is the SDR role as it will exist in 2030. You direct AI agents, automate your own workflows, and apply human judgment exactly where the machines stall. We call it being the human in the loop for top-of-funnel growth, and Harper is one of the few places in the world actually building it. The primary job is AI-native outbound: sourcing new business owners from enriched public data, running call and email campaigns at volume not possible 3 years ago, and converting cold contacts into real opportunities. Alongside that, you own an inbound pipeline: working a power dialer of warm leads our AI agents couldn't reach, completing intake applications live on the phone, and warming up quoted leads and transferring them to the account executive (AE) team. The best performers here don't stay SDRs. This is a deliberate first step into a sales and go-to-market career. WHAT YOU'LL DO - Run outbound at serious volume. Cold-calls, email sequences built with our marketing team, and follow-ups. You're the first voice of Harper. Rejection is part of the rhythm. Complete intake on the call. Learn what a business does, what risk it carries, and capture everything, in minutes, not hours. Build with AI, not just alongside it. You'll use AI agents to automate your own sequencing, data entry, and reporting. Every workflow you automate becomes permanent Harper infrastructure. Partner with marketing. You're their human in the loop: feeding back what messaging lands on calls, which ad-sourced leads convert, and which segments respond. Hit volume and quality targets, both. You're measured on new leads brought in, lead conversion, completed applications, and AE transfers. You don't trade accuracy for speed or speed for accuracy. WHO YOU ARE - An ambitious and personable recent grad or early-career candidate who is excited to launch a career in GTM sales. - Excited to join the sales team at a hyper-growth AI startup disrupting the insurance industry. - You've worked a high-volume phone role and were good at it, or you haven't, but everyone who knows you is sure you would be. - Rejection doesn't rattle you. - Talking to people all day energizes you. Call 50 gets the same energy as call 1. - You reach for AI tools by instinct. When something is repetitive, your first thought is to automate it. - You don't need hand-holding. You need a shot. THE REALITY: READ THIS BEFORE YOU APPLY This is a high-volume outbound role, on-site in San Francisco, Monday through Friday, 8am to 8pm ET, in the building with the team. But if you're the kind of person who gets sharper as the day goes on, this is one of the fastest paths into tech sales. You'll learn an entire industry from the inside, work at an AI-native company that's actually shipping, and help define what top-of-funnel growth becomes over the next decade. COMPENSATION & LOGISTICS - Salary: $80,000–$135,000 OTE based on experience; higher for top performers. - Location: On-site, San Francisco. Full-time, in-office. - Schedule: Monday–Friday, 8am–8pm ET. BENEFITS - Uber commuter benefits - Meals provided: breakfast, lunch, and dinner - Snacks, drinks, and coffee stocked daily - Free gym membership - Health, dental, and vision insurance REQUIREMENTS - Fluency in fast-paced, demanding environments (new grads OK) - Strong multitasking ability: talk, listen, and log simultaneously - Professional, confident, and clear on the phone - Based in San Francisco, in-office, full-time NICE TO HAVE - Insurance, fintech, or financial-services background - Bilingual+ - SDR or BDR roles at high-volume SaaS or AI companies - Outbound or customer-success-focused experience PROCESS We run a tight process and move fast, because that's how we operate. 1. AI phone screen. A live role-play sales simulation. 2. Fit and alignment call. Who you are, what drives you, and whether Harper is the right environment for you to do the best work of your life. 3. Super day. 3 to 4 hours on-site: case exercises, a live cold call simulation, hands-on work with the team, and a real look at what it means to build at this level. As much for you as for us. TO APPLY Send your resume and tell us about the highest-rejection stretch of work you've ever pushed through, and why you kept dialing.